Classifications

• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
  • C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
  • C10M137/04—Phosphate esters
  • C10M137/10—Thio derivatives
  • C10M137/105—Thio derivatives not containing metal
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
  • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
  • C07F9/02—Phosphorus compounds
  • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
  • C07F9/6536—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and sulfur atoms with or without oxygen atoms, as the only ring hetero atoms
  • C07F9/6539—Five-membered rings
  • C07F9/65392—Five-membered rings containing two nitrogen atoms
  • C07F9/65395—Five-membered rings containing two nitrogen atoms having the two nitrogen atoms in positions 1 and 2
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
  • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
  • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
  • C10M2203/102—Aliphatic fractions
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/28—Esters
  • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/28—Esters
  • C10M2207/287—Partial esters
  • C10M2207/289—Partial esters containing free hydroxy groups
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/28—Esters
  • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
  • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
  • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
  • C10M2215/26—Amines
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
  • C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
  • C10M2217/046—Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
  • C10M2217/06—Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/02—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds
  • C10M2219/022—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds of hydrocarbons, e.g. olefines
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
  • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
  • C10M2219/083—Dibenzyl sulfide
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
  • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
  • C10M2223/04—Phosphate esters
  • C10M2223/045—Metal containing thio derivatives
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
  • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
  • C10M2223/04—Phosphate esters
  • C10M2223/047—Thioderivatives not containing metallic elements
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2010/00—Metal present as such or in compounds
  • C10N2010/04—Groups 2 or 12
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
  • C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2070/00—Specific manufacturing methods for lubricant compositions
  • C10N2070/02—Concentrating of additives

Definitions

• a compound, suitable for use as a lubricant additive is an oil-soluble reaction product of a di-(organo) dithiophosphoric acid, wherein the organo groups are aliphatic moieties, and a 1,3,4-thiadiazole of the general formula:
• This invention relates to certain novel lubricant addi-' tives, more particularly to certain additives useful, inter alia, as corrosion inhibitors.
• 2,5-di-mercapto-l,3,4-thiadiazole and numerous de' rivatives thereof have been proposed, and in the case of certain derivatives, widely used, as corrosion inhibitors, particularly for inhibiting corrosion of copper, in lubricants.
• An improvement in the usefulness of this class of lubricant additive has now been made by preparing certain novel derivatives of 2,5-di-mercapto- 1,3,4-thiadiazole which have corrosion inhibiting properties and in addition a degree of activity as antioxidant and load carrying additives,
• the present invention provides a compound, suitable for use as a lubricant additive, which compound is an oil-soluble reaction product of a di- (organo) dithiophosphoric acid, wherein the organo groups are aliphatic moieties, and a 1,3,4-thiadiazole of the general formula:
• X is a hydrogen atom or the residue of an ethylenically unsaturated alcohol, carboxylic acid, anhydride, amide or imide, the reaction of the di-(organo) dithiophosphoric acid and the 1,3.4-thiadiazole being carried out in the presence of an oxidising agent.
• the present invention also provides an oil-soluble compound. suitable for use as a lubricant additive, which compound has the general formula:
• the organic moieties desirably should not be too large as this reduces the portion of the molecule constituting the active portion, i.e. which imparts the desired corrosion inhibiting and/r antioxidant properties, and leads to a need for large dosage weights to be used in order to impart the desired properties.
• the organic moieties may, but preferably do not, bear one or more inert substituents such as alkoxy groups.
• Preferred organic moi eties are alkyl groups containingg from 3 to 18, more preferably 3 to 10, carbon atoms, and they are preferably primary or secondary alkyl groups, particularly the latter.
• the two organic moieties may be the same.
• A1- ternatively, a mixture of organic moieties can be employed by using a dithiophosphoric acid containing two different organic groups and/or by using a mixture of two or more different dithiophosphoric acids.
• the 2,5-di-mercapto-1,3,4-thiadiazole may be condensed with an ethylenically unsaturated alcohol or carboxylic acid, preferably containing from 4 to 18 carbon atoms, or an ethylenically unsaturated anhydride, imide or amide of a carboxylic acid.
• the anhydrides, imides and amides so used are preferably derivatives of a carboxylic acid containing from 4 to 18 carbon atoms. The condensation may be readily carried out by heating the co-condensantstogether at a suitable temperature.
• the rate of condensation is unacceptably low whereas at too high a temperature the condensation may be deleteriously affected by decomposition of the 1,3,4-thiadiazole and other undesirable side-reactions. Accordingly, we prefer to use a temperature of from 120 to 160C., with about 140C usually being the optimum temperature.
• the condensation may be, but preferably is not, carried out in the presence of an inert solvent such as xylene.
• the present invention also includes, in a further aspect, the process which comprises reacting a di- (organo) dithiophosphoric acid, wherein the organo groups are aliphatic moieties, and a 1,3,4-thiadiazole of the general formula:
• thiadiazole 2 dithiophosphate groups, substituted via a sulphur atom, on each 1,3,4-thiadiazole nucleus.
• lt is possible for an excess of either reactant to be present during the reaction, except in the case where it is desired to react only one of the mercapto groups of 2,5- di-mercapto-l,3,4-thiadiazole.
• the coreactants are used in substantially stoichiometric proportions required to substitute the desired number of dithiophosphate groups 1 or 2) on the 1,3,4- thiadiazole nucleus.
• the reaction temperature employed in the process of the present invention is preferably not more than C more preferably not more than 50C.
• the oxidising agent employed may be a peroxide, hydrogen peroxide being particularly preferred.
• a peroxide oxidising agent it may be convenient to use a slight excess over the stoichiometric amount required.
• An extremely useful procedure is to add a slight, e.g. 10%, excess of aqueous hydrogen peroxide to a mixture of the 1,3,4- thiadiazole and the dithiophosphoric acid.
• the resulting exotherm raises the temperature of the reaction mixture and the temperature is preferably controlled, e.g. by cooling, so that it does not rise above 50C. When the exotherm ceases, the reaction is substantially complete.
• the present invention also provides lubricating compositions comprising a major amount of a lubricating oil and a minor amount of one or more additives of the present invention.
• the amount of the additives of the present invention which is employed is preferably from 0.001 to 10% by weight based on the total weight of the composition. Within this range the most preferred amounts depend on the primary function of the additive. When used primarily as a corrosion inhibitor from 0.01 to 0.5% by weight, based on the total weight of the compositions, is especially suitable. However, when the primary function is as an antioxidant, larger amounts are preferably used, such as from 0.25 to 2.0% by weight, based on the total weight of the composition.
• the lubricating compositions of the present invention may also contain, if desired, conventional lubricant additives such as ancillary antioxidants and corrosion inhibitors, antiwear additives, dispersants, particularly dispersants of the succinimide type, detergents, thickeners, pour-point depressants and viscosity index improvers.
• conventional lubricant additives such as ancillary antioxidants and corrosion inhibitors, antiwear additives, dispersants, particularly dispersants of the succinimide type, detergents, thickeners, pour-point depressants and viscosity index improvers.
• additive concentrates comprising a minor amountof a lubricating oil and a major amount of one or more additives in accordance with the present invention
• additive packages comprising a minor amount of a lubricating oil and a major amount of a combination of one or more additives in accordance with the present invention and at least one other lubricant additive.
• the lubricating oil used in the lubricating compositions of the present invention may be any of the well known synthetic ester oils, such as dioctyl sebacate.
• the preferred oils are mineral oils of lubricating viscosity of well known type.
• EXAMPLE 1 0,0'-Dicapryl (l-methyl heptyl) dithiophosphoric acid (806g, 0.2m), 2,5-dimercapto-l,3,4-thiadiazole (g, 0.1m) and ethanol (500ml) were stirred together to give a clear solution and 15g (0.22m) ofa 50% aqueous hydrogen peroxide solution was added thereto dropwise at a rate such that the resulting exotherm did not raise the temperature of the reaction mixture above 50C.
• the final product was a yellow oily liquid (39.5g) containing 4.36%N.
• EXAMPLE 3 50% hydrogen peroxide (13.6g, 0.2 mole) was added dropwise with cooling and stirring to 0,0-diisobutyl dithiophosphoric acid (51.2g, 0.2 mole) 2,5-dimercapto- 1,3,4-thiadiazole (15g, 0.1 mole) ethanol (25 ml) and water (34ml). During the addition the temperature was not allowed to rise above 50C.
• the product was obtained in a yield of 60g and contained 1.75%N.
• EXAMPLE 5 50% hydrogen peroxide (15.0g, 0.22mole) was added dropwise to 0,0'-di-2-ethylhexyl dithiophosphoric acid (45g, 0.11 mole), 2,5-dimercapto-l,3,4- thiadiazole (15g, 0.1m) and 0,0'-di-isobutyl dithio phosphoric acid (28.8g, O.l1mole) in 50% ethanol ml).
• the addition was complete the mixture was refluxed for l hour, 200 ml petroleum ether (B. Pt. 6268C.) added, the mixture left overnight and then filtered, 8.2g of solid being removed. The organic layer was washed with water, then the petroleum ether distilled off to yield 74g of a liquid which contained 3.14%N and which went cloudy on standing.
• EXAMPLE 8 A product was preparedfrom a sample of 0,0-diallyl dithiophosphoric acid of equivalent weight 243 (theory 210). The product was prepared as in Example 2 using the following reactants:
• Example 13 was repeated substituting 0,0-diisopropyl dithiophosphoric acid (52.8g, 0.2mole) for the 0,0-di-isopropyl/1,3-dimethy1 butyl dithiophosphoric acid. The yield was 95g of a red liquid which contained 3.96%N.
• Corrosion inhibiting properties were determined by Copper Strip tests and Silver Corrosion tests.
• Copper Strip test strips of copper were immersed for 3 hours at 120C in a test blend consisting of a base oil having dissolved therein O.l% by weight of the inhibitor under test and 2% dibenzyl disulphide, the latter being a source of active sulphur acting as a corrosive agent.
• the base oil used was either a 150 Solvent Neutral mineral oil of viscosities about 33 and 5.3cSt at F and 210F respectively; a dibasic acid ester of viscosities about 12.5 and 3.3cSt at 100F and 210F respectively or a pentaerythritol tetraester of viscosities about 26 and 5cSt at 100F and 2lOF respectively.
• After immersion the strips were removed, examined visually and a demerit rating assigned according to the degree of staining of the strip (ASTM standards). The results of these tests are shown in the following Table 2.
• Silver Corrosion tests were also carried out, by a modification of the test described in US. Pat. No. 2,719,126.
• Square silver plates measuring approximately l.5cm X l.5cm having a hole in one corner, were polished with 600 mesh carborundum and suspended by wire for 24 hours at a temperature of C in a 75g sample of the same mineral oil test blend as used in the Copper Strip tests reported in Table 2.
• the silver plates were visually examined, washed with petroleum ether (B.Pt. 6268C.), immersed in 10% potassium cyanide until clean, washed with water, washed with acetone and the weight loss during the test determined.
• the results of these tests are shown in the following Table 4.
• Antiwear properties of the additives of the present invention were determined by means of the Timken O.K. load test in accordance with the Institute of Petroleums Test Method 1P/240/69.
• the apparatus employed comprises a roller mounted on a spindle, the roller being rotated against a seated metal block lubricated with the test blend.
• a lever system mounted on the spindle is a lever system to one end of which is applied a weight, the weight being increased until the test blend fails as judged by scoring of the seated metal block.
• the blends consisted of the test additive dissolved in the same mineral base oil as used in the Copper Strip tests.
• the results of the Timken OK. load tests are shown in the following Table 5.
• Antioxidant properties of the additives of the present invention were measured by Rotary Bomb Tests carried out in the manner described in the left-hand column of page 220 of the article entitled, Evaluation of Antioxidants for Automotive Lubricants Using the R0- tary Bomb" in the Journal of the Institute of Petroleum, Vol 55, No. 544, July 1969, pages 219 to 226. The tests were carried out at C, with water present as described in the aforementioned article. The blends tested consisted of 0.5% by weight of the additive under test dissolved in a 500 Solvent Neutral mineral oil and 210F respectively, and the results obtained are shown in the following Table 6.
• a compound, suitable for use as a lubricant additive which compound is an oil soluble reaction product of a di-(organo) dithiophosphoric acid, wherein the organo groups are alkyl or alkenyl of 3 to 18 C atoms, 0ptionally containing an alkoxy substitucnt, and a 1,3,4-
• thiadiazole selected from the group consisting of 2,5- dimercapto-l,3,4-thiadiazole and a compound resulting from the condensation reaction of 2,5-dimercapto- 1,3,4-thiadiazole at a temperature in the range of about 120-160C with a compound selected from the group consisting of alkenols and alkenoic acids of 4 to 18 carbon atoms and the anhydrides, amides and imides thereof, the reaction of the di-(organo) di-thiophosphoric acid and the 1,3,4-thiadiazole being carried out in the presence of a peroxide oxidizing agent.
• a compound according to claim 1 wherein the or gano groups are alkyl of 3 to 18 C atoms or alkyl and wherein the ethylenically unsaturated compound with which the 2,5-dimercapto-l,3,4-thiadiazole may be reacted is selected from the group consisting of alkenyl alcohols, alkenyl carboxylic acids and alkenyl carboxylic acid anhydrides.
• a compound according to claim 1 wherein the organo groups are alkyl of 3 to 18 C atoms or allyl and wherein the di-(organo) dithiophosphoric acid is reacted with 2,5-di-mercapto-l,3,4-thiadiazole.
• a compound according to claim 1 wherein the organo groups are alkyl of 3 to 18 C atoms or allyl and wherein the di-(organo) dithiophosphoric acid is reacted with a condensation reaction product of 2,5- dimercapto-l,3,4-thiadiazole with a compound selected from the group consisting of oleic acid, crotonic acid, oleyl alcohol and dodecenyl succinic anhydride.
• a compound according to claim 1 wherein the organo groups of the di-(organo) dithiophosphoric acid are the same or different and at least one is an alkyl group containing from 3 to carbon atoms.
• a compound according to claim 1 wherein the oxidising agent is hydrogen peroxide.
• a process for preparing a compound suitable for use as a lubricant additive comprises reacting at a temperature of not more than C a di- (organo) dithiophosphoric acid, wherein the organo groups are alkyl or alkenyl of 3 to 18 C atoms, optionally containing an alkoxy substitutent, and a 1,3,4- thiadiazole selected from the group consisting of 2,5- dimercapto-l,3,4-thiadiazole and a compound resulting from the condensation reaction of 2,5- dimercaptol,3,4-thiadiazole at a temperature in the range of about 160C with a compound selected from the group consisting of alkenols and alkenoic acids of 4 to 18 carbon atoms and the anhydrides, amides and imides thereof; the reaction of the di-(organo) dithiophosphoric acid and the 1,3,4-thiadiazole being carried out in the presence of a peroxide oxidizing agent to form an oil-soluble reaction product.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Chemical Kinetics & Catalysis (AREA)
• General Chemical & Material Sciences (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Health & Medical Sciences (AREA)
• Life Sciences & Earth Sciences (AREA)
• Biochemistry (AREA)
• General Health & Medical Sciences (AREA)
• Molecular Biology (AREA)
• Lubricants (AREA)
• Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)

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Cited By (18)

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• 1972
  • 1972-04-25 GB GB1904872A patent/GB1428656A/en not_active Expired
• 1973
  • 1973-04-13 CA CA168,691A patent/CA1014961A/en not_active Expired
  • 1973-04-16 US US351459A patent/US3914241A/en not_active Expired - Lifetime
  • 1973-04-20 IT IT23344/73A patent/IT984085B/it active
  • 1973-04-24 NL NL7305713A patent/NL7305713A/xx unknown
  • 1973-04-24 DE DE2320644A patent/DE2320644A1/de active Pending
  • 1973-04-24 FR FR7314794A patent/FR2182008B1/fr not_active Expired
  • 1973-04-24 BE BE130326A patent/BE798610A/fr unknown
  • 1973-04-24 JP JP48047171A patent/JPS4947402A/ja active Pending

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